N-[(1,1-二甲基乙氧基)羰基]-L-酪氨酰-L-亮氨酸苄酯 | 72210-21-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-[(1,1-二甲基乙氧基)羰基]-L-酪氨酰-L-亮氨酸苄酯
• 英文名称: Boc-Tyr-Leu-OBzl
• 英文别名: N-t-butyloxycarbonyl-L-tyrosyl-L-leucine benzyl ester；Boc-Tyr-Leu-OBn；Boc-Tyr-Leu-OCH2Ph；benzyl (2S)-2-[[(2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-4-methylpentanoate
• CAS: 72210-21-0
• 化学式: C₂₇H₃₆N₂O₆
• 分子量: 484.593
• InChiKey: SVINFKSLOMLCGB-GOTSBHOMSA-N

物化性质

• 沸点：
  672.7±55.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(1,1-二甲基乙氧基)羰基]-L-酪氨酰-L-亮氨酸苄酯 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 Boc-Tyr-Leu-OH
  参考文献：
  名称：

  Incorporation of fluoroprolines to proctolin: Study on the effect of a fluorine atom toward peptidic conformation

  摘要：

  In spite of quite small steric perturbation, substitution of proline (Pro) in the target pentapeptide proctolin (Arg-Tyr-Leu-Pro-Thr) for (4R)- as well as (4S)-4-fluoroproline led to apparent alteration of the pyrrolidine ring structure which eventually resulted in the significant conformational change of the whole molecules which was assumed on the basis of their NOESY spectra. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2007.12.005
• 作为产物：
  描述：

  Boc-L-酪氨酸 、 L-亮氨酸苄酯对甲苯磺酸盐 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以49%的产率得到N-[(1,1-二甲基乙氧基)羰基]-L-酪氨酰-L-亮氨酸苄酯
  参考文献：
  名称：

  肽氯甲基酮的合成及其对人脾纤溶酶（SFP）和人白细胞弹性蛋白酶（LE）的抑制作用。

  摘要：

  为了比较人脾纤溶酶（SFP）和人白细胞弹力酶（LE）的性质，通过传统方法合成了多种来自底物的氯甲基酮，旨在获得对这两种酶具有特异性和强效的不可逆抑制剂。在各种肽氯甲基酮中，发现Boc-Ala-Tyr-Leu-Val-CH2Cl对SFP和LE表现出最有效和特异的抑制作用。这两种酶都被C-末端具有Val残基的肽氯甲基酮以类似方式抑制，这表明SFP和LE之间存在相似性。

  DOI：

  10.1248/cpb.35.3576

文献信息

• Synthesis of peptide chloromethyl ketones and examination of their inhibitory effects on human spleen fibrinolytic proteinase(SFP) and human leukocyte elastase(LE).
  作者：YUKO TSUDA、YOSHIO OKADA、YOKO NAGAMATSU、UTAKO OKAMOTO

  DOI：10.1248/cpb.35.3576

  日期：——

  Various substrate-derived chloromethyl ketones were synthesized by a conventional method for the purpose of obtaining specific and potent irreversible inhibitors for human spleen fibrinolytic proteinase (SFP) and human leukocyte elastase (LE) in order to compare the properties of SFP with those of LE. It was found that Boc-Ala-Tyr-Leu-Val-CH2Cl among the peptide chloromethyl ketones exhibited the most effective and specific inhibition of SFP and LE. The two enzymes were inhibited by peptide chloromethyl ketones having a Val residue at the C-terminus in a similar manner, demonstrating a similarity between SFP and LE.

  为了比较人脾纤溶酶（SFP）和人白细胞弹力酶（LE）的性质，通过传统方法合成了多种来自底物的氯甲基酮，旨在获得对这两种酶具有特异性和强效的不可逆抑制剂。在各种肽氯甲基酮中，发现Boc-Ala-Tyr-Leu-Val-CH2Cl对SFP和LE表现出最有效和特异的抑制作用。这两种酶都被C-末端具有Val残基的肽氯甲基酮以类似方式抑制，这表明SFP和LE之间存在相似性。
• Synthesis and effects of two peptide fragments of thymopoietin II on E-rosette forming cells in the uremic state.
  作者：TAKASHI ABIKO、MIHOKO KUMIKAWA、HIROSHI SEKINO

  DOI：10.1248/cpb.27.2233

  日期：——

  Two peptides, H-Lys-Asp-Val-Tyr-Val-Gln-Leu-Tyr-Leu-OH and H-Arg-Lys-Asp-Val-Tyr-Val-Gln-Leu-Tyr-Leu-OH (fragment of thymopoietin II), were synthesized in a conventional manner utilizing the hydrogen flluoride procedure, and were tested to determine their effects on E-rosette forming cells in the uremic state. The synthetic decapeptide increased E-rosette forming capacity in the presence of uremic serum. The synthetic nonapeptide had no effect on the E-rosette formation inhibiting activity of uremic serum.

  两种肽，H-Lys-Asp-Val-Tyr-Val-Gln-Leu-Tyr-Leu-OH 和 H-Arg-Lys-Asp-Val-Tyr-Val-Gln-Leu-Tyr-Leu-OH（片段胸腺生成素 II)，利用氟化氢程序以常规方式合成，并进行测试以确定它们对尿毒症状态下 E-玫瑰花结形成细胞的影响。合成的十肽增加了尿毒症血清存在下 E-玫瑰花结的形成能力。合成的九肽对尿毒症血清的E-玫瑰花结形成抑制活性没有影响。
• Siemion, Ignacy Z.; Klis, Wieslaw A.; Nawrocka, Eleonora, Polish Journal of Chemistry, 1981, vol. 55, # 10, p. 2219 - 2222
  作者：Siemion, Ignacy Z.、Klis, Wieslaw A.、Nawrocka, Eleonora

  DOI：——

  日期：——
• TSUDA, YUKO;OKADA, YOSHIO;NAGAMATSU, YOKO;OKAMOTO, UTAKO, CHEM. AND PHARM. BULL., 35,(1987) N 9, 3576-3584
  作者：TSUDA, YUKO、OKADA, YOSHIO、NAGAMATSU, YOKO、OKAMOTO, UTAKO

  DOI：——

  日期：——
• Incorporation of fluoroprolines to proctolin: Study on the effect of a fluorine atom toward peptidic conformation
  作者：Takamasa Kitamoto、Taeko Ozawa、Megumi Abe、Shunsuke Marubayashi、Takashi Yamazaki

  DOI：10.1016/j.jfluchem.2007.12.005

  日期：2008.4

  In spite of quite small steric perturbation, substitution of proline (Pro) in the target pentapeptide proctolin (Arg-Tyr-Leu-Pro-Thr) for (4R)- as well as (4S)-4-fluoroproline led to apparent alteration of the pyrrolidine ring structure which eventually resulted in the significant conformational change of the whole molecules which was assumed on the basis of their NOESY spectra. (C) 2008 Elsevier B.V. All rights reserved.